Femboy High Ch. 01

All characters presented in this story are 18 years of age or older

Chapter 1--Josh

I don't know how to start this story without saying I'm not gay, and that I've never done any gay stuff in my life. That being said, there is a guy in my class named Alex Reynolds who is hotter than any of the girls at my school. When we started senior year, Alex came back wearing a girl's uniform. We go to St. Igneos University, a very expensive and exclusive private high school in Mentor, Ohio. St. Igneos costs $17,000 per year and is one of the most expensive schools in the state.

Not to get off track, but this story only makes sense in the confines of our elite private school. I know Alex comes from rich parents. His mother's a doctor and his dad's a lawyer. My parents both work at Progressive insurance as associates. We have money, but we're not rich. I have a younger sister in middle school and an older brother in college right now. The only reason I'm going to St. Igneos is because of an athletic scholarship. Yes, private schools really do have athletic scholarships. It's the reason private schools win a lot of regional championships. They literally draft the best athletes from middle schools and intramural sports programs. I play lacrosse for St. Igneos. If I don't perform, I can't stay in school.

St. Igneos isn't just a flashy, expensive school. The school boasts a 100% graduation rate and 92% college enrollment rate. I know that sounds impossible, but I've never known a student who dropped out. Every student gets their own tutor, nutritionist, and therapist. Classes are taught in person, but homework is done on the thousand dollar laptops we get when we start freshman year.

All of this is to say, at any other school, I'm sure everyone would give Alex a hard time. Not only does he wear the girls' uniform, but he has long hair and wears makeup. He could easily pass as a girl. At St. Igneos, there's bullying like in every school, but not to the level you see in TV or movies. The thing about having rich parents is, everyone is very eager to sue. If you learn anything from me, know that rich people love suing people. Because of weekly therapy, access to financial and pharmaceutical resources, teaching aids, etc., everyone's fairly well adjusted...as well as you can be in high school.

Other than that, it's a pretty normal school. Everyone's planning for the weekend. We text, video chat, snapchat, skype chat, sometimes even call each other. It seems like everyone wants to be a Youtuber now, and we even have an elective digital media class after the parents petitioned for it. Everyone's horny all the time which can be frustrating. There's a party every weekend, and everyone's stressed about ACT's, SAT's, and plans for college.

I turned 18 just when school started, and to my simultaneous relief and agony, I also learned Alex was 18 and single, meaning he was available. It's not enough to say Alex looks like a girl. He looks like an insanely hot girl. His legs are milky and pale with a little thickness. His hair is dark and thick. His face...fuck. Pouty lips, intense eyes...just want to see those lips wrapped around my cock so bad. That little bubble butt. I just want to yank his panties down, lift his skirt up, and bury my cock balls-deep in his ass. I can't control myself when I see him. It doesn't help he posts bikini pics on Instagram where I follow him on an alt account. I've never felt the same way about a girl as I do about Alex. It's like this fire or animal inside me, feel like I'm on drugs. I've never been attracted to a guy in my entire life before Alex.

Despite Alex being immensely fuckable, sometimes the kids at school give him a hard time. At private schools, bullying is super passive aggressive. You can't call people slurs or beat them up or else lawyers get involved fast. It's always suggestive and stealthy. Insinuations, stealing their things out of their locker, leaving mean notes for them to find. I mean, Alex is fucking brave for coming to school dressed like a girl. None of the other guys can claim to be that tough.

I initially though Alex was trans and I'd have to hook up with her, but I stealthily asked around and found out he doesn't consider himself trans. I don't know why he dresses like a girl but doesn't consider himself a girl, but then again there's a lot of things I don't understand. I don't want to be in a gay relationship, but I also want to try and get Alex's butt pregnant. I want to fuck him so bad, but I'm terrified of what everyone would say.

As I said, I play lacrosse, and the thing about being on a sports team is you think everyone would be friends with each other, but that's not really the case. There's freshmen, junior varsity, and varsity teams that almost never interact except for scrimmaging. My best friend's name is Donald who also plays lacrosse. He's the only black kid at the school and got in on an athletic scholarship just like me. We both come from middle income families and we're able to bond over the weird stuff rich kids get into. Like for example, rich kids are really into pills and cocaine. Some smoke weed, but that's considered kind of low class. I guess because it stinks up the house or car and leaves resin unless you smoke it out of a beer can which is pretty white-trash.

Before you join the school, you have to sign a pledge saying that you will not drink, smoke, do drugs, cheat on tests or homework, or have pre-marital sex. Every student has to sign the agreement to attend classes, and as far as I know, everyone ignores it. I get drunk every Friday and Saturday night. There's always a party. There's always a house where rich parents are out of town. I've had Donald over my house, but I've never had any of my rich friends over. Everyone just assumes me and Donald are rich like them. When I tell them my parents work at Progressive, they just assume they're CEO's or something.

But anyway, back to Alex. He just shows up the first day of senior year in that uniform and immediately makes me question my sexuality. I ran into Alex once or twice at parties but never really hung out with him before senior year. He was always known as the gay kid at school even though there's like a dozen gay kids in the senior class alone, and two trans kids. I know the trans kids don't like Alex because he crossdresses but says he's not trans. He was always pretty quiet and I never for a second considered him sexually appealing. You think gay and trans kids would have a hard time at a religious private school, but the religious stuff is really toned down. I think it's just a front for tax exempt status.

Ever since Alex started dressing girly, I can't stop thinking about him. Stalking his Instagram and shamefully masturbating to the horrible things I'd do to his tight, little body. Just wear him out, break him in half before I shove my cock down his throat and empty my balls in his stomach.

When you're 18 and an athlete, you're just horny all the time. You have elevated testosterone, and girls are usually into you unless you're a wrestler or a lineman in football. I've fucked girls. I've dated. I'm very much straight and was constantly thinking about girls before Alex showed up and confused everything. I wasn't angry at him. I was frustrated with myself.

I did my best to avoid Alex at school because whenever I would see him, I would just get totally flustered and horny. And the thing is, I've never been like that around girls. I'm good at talking to girls. I've turned girls down. But just seeing Alex makes me feel so stupid like I could blurt out something gay at any moment.

At least I had lacrosse and homework to fixate on instead of thinking about Alex all day. That was until Alex joined the damn cheerleading squad. There were already two male cheerleaders at the school, and it wasn't even a big thing. No one cared. Yes, they were both gay if you were wondering. Then one practice, Alex showed up wearing a cheerleader's uniform.

The lacrosse team has its own field to practice on. There's actually three lacrosse fields: one for freshmen, junior varsity, and the varsity team. I was varsity. The field was equipped with massive bleachers and an arena sized LED board. I loved being on the lacrosse field. Felt like the most natural place on earth. That was until Alex walked out in a cheerleader uniform. The cheerleading team always used the football or lacrosse field when practicing. Before Alex, I never understood the sexual appeal of cheerleaders. Either a girl is hot or she isn't. I always felt the cheerleader fetish was for creepy, old men who want women to dress like children. Anyway, Alex showed up and I couldn't practice. Was simply too distracted by him in that short, pleated skirt. Blue, silver, and black pleats--the school's colors.

After a few practice plays where I screwed up everything, Coach Hemmer (Hammer if you're afraid of him, Hummer if you're not) made me run laps around the track. This made things even worse. I would have to pass by the cheerleaders while hiding half a chub in my baggy lacrosse shorts. I practically sprinted to get it over with as fast as possible.

As I came around the curve where the cheerleader's were practicing, they all started to stop and look my way. Of course I got their attention. A 6'2" jock comes sprinting at you, you'll probably watch to see what he's doing. I try to look at all their faces at once, but my eyes kept shifting back to Alex. His eyeshadow was done up in the school's colors even though it was just practice. I smiled nervously as I approached, and the squad parted to let me through. All the girls (and guys) were smiling bashfully as I ran past them. I tried not to look directly at Alex. It was over in a second, but as I ran past, I heard a guy ask "who was that?"

Practice went for two hours, and it wasn't long before I was watching Alex again. The cheerleaders were practicing high kicks and Alex could kick with the best of them. Then he turned around with the squad and was kicking towards the lacrosse team. Normally every cheerleader wears these thick, fleece panties to cover up their underwear, but not Alex. They must not have issued him a pair yet. Instead, he was either knowingly or unknowingly flashing the entire team his tiny bulge behind a pair of white, striped panties. The entire team stopped at that point, probably not realizing, or maybe not caring Alex identified as a guy. The defensive coordinator ran over to the cheerleading coach and explained what was happening, but not without Steve and Tony shouting to let the cheerleaders practice.

Practice couldn't end soon enough, and wouldn't you know, Alex came in the boy's locker room just as we were wrapping up. Without a hint of self-consciousness, he started to undress in front of everyone. Most the guys stopped to watch. I tried to continue without staring directly at him.

"What are you fags looking at?" Alex said when he looked up to see everyone watching him. Some of the guys turned away, but a few others, like Dominic, kept staring like a creep.

"They won't let you change in the girl's room?" said Arthur, the team captain. Arthur was definitely a future politician, maybe even president. He had this way of talking where he could convince you of anything. He was nice to everyone, did martial arts, had a steady girlfriend, got perfect grades, and partied his ass off every weekend.

"I'm not a girl," Alex said, stripping down to his panties. I couldn't help but look. His little package was sealed like a gift behind a thin piece of cotton. All I could think about was snatching his underwear so me and the entire team could run a train on him.

"If you want, next time we could wait outside while you change first," said Arthur, speaking for the team.

"Thanks, but I've been changing in front of guys since middle school."

Was Arthur hitting on him? Arthur was a nice guy, but he seemed to be really going out of his way for Alex. I was forced to lean against my locker to hide my erection when Alex bent over to change his socks. That fucking round little butt perfectly covered by his panties. I was literally gripping the door of my locker to stop myself from tackling him and forcing myself inside that tight little butt. This fucking little princess was turning me gay, and I couldn't stop it.

Dominic had less self-control than me as he passed Alex and slid the edge of his hand up Alex's crack, making a "cha-ching" sound and grinning like an asshole. Some of the guys laughed. Not Alex who shot up looking furious and kicked Dom right in the cock. Dominic grabbed Alex by the throat and slammed him against the lockers, cradling his sore balls with his other hand.

"No fags allowed in the men's room," Dominic growled. Dominic probably had eighty pounds and a solid foot on him.

"That's enough," said Arthur, grabbing Dominic's shoulder and yanking him away before I could intervene.

"Was just fooling around," said Dom, his hands up in surrender. Arthur would easily kick the shit out of him. 6'5", black belt in jiu-jitsu. Wouldn't even be a fight.

"You do anything like that again, and you're off the team."

"You don't decide who's on the team," said Dom, stepping to him. That same air fell over the locker room like when a fight was about to break out at a party. The whole team was there to pull them apart just in case.

"You have any idea who his dad is? He'd sue your family into the fucking ground. You'd be lucky you weren't expelled before it was all over. Now back the fuck off," said Arthur, giving Dom a hard shove. It was definitely the most non-sexual tension I had ever felt, and I was not looking forward to breaking up a fight between these two beasts. Guess cute boys have that effect on guys. A couple guys left, but most wanted to see the fight. Instead of a brawl, Dom gave everyone a hateful look and stormed out. Arthur watched him leave.

"You okay?" said Arthur, leaning over Alex, almost cornering him against the lockers. Alex pushed past him wearing only panties and one of those tank tops with shoulder straps girls wear, and went into the hall. Guess the hall would be mostly empty after five. It did really seem like Arthur had a thing for Alex. And not to be gay, but Arthur was a good looking guy. I mean we were all pretty cut, but Arthur had like good looks and a nice way of talking. Alex would probably be crushing on him in a week.

As everyone cleared out of the locker room, Donald told me to hit him up when I got home, and I nodded as he left. As I was leaving, I saw a little bag like a purse under the bench by Alex's locker. I picked it up and saw it was filled with makeup. My little sister had one just like it. It had to belong to Alex. I hurried out to the hall, but he was already gone. I could have just left it in the office and they'd have him come up during morning announcements, but this seemed like an opportunity to talk to him tomorrow.

As soon as I got home I had to rub one out to Alex. I thought about him standing there in the locker room in nothing but his panties as everyone gathered around him. Someone would rip his panties off, then we'd all take turns on him. Alex would have to suck everyone's cocks. Some of the guys would be really rough and fuck his throat. He'd act all grateful for just being allowed to blow the lacrosse team. I'd be really gentle and let him enjoy sucking my cock. Stroke his hair, caress his face, make him look at me while I was down his throat, those pink lips stretched around my cock. He'd be so pretty.

After everyone took turns using his mouth, we'd bend him over the bench and run a train on him. Each guy taking turns in his tight little hole, pumping him full of cum. Alex was easily smaller than anyone on the team and would have to take every cock. When it was my turn I'd fuck the living shit out of him, stroke his little cock until he came on the floor. He'd be the team's bitch.

As far as I knew, no one on the team was gay, but I felt like Alex would be down servicing all of us, especially as some kind of cheerleader duty. Apparently there was a girl who attended St. Igneos right before my freshman year, and the entire football team gangbanged her after they won regionals. Really wish I knew what her name was. I'd love to do something like that with Alex. I mean, if he dressed like a girl, clearly he wanted attention from guys. What's better than being the center of attention? After everyone made him a little cum dumpster, I'd carry him to the showers and clean him up. Maybe kiss him. God, that was gay thinking about kissing a boy, but as far as I was concerned, Alex did not count. Like I said, I've never found a guy attractive in my life. Like, I can recognize when a dude is good looking, but I've never wanted to kiss a guy or anything. Alex just seemed to have that affect on guys.

Regardless, it was an insanely hot fantasy, and I ended up masturbating four times that night thinking about Alex. If he showed up again tomorrow, I would get to see him in panties again. There's no way I could function seeing him everyday in his underwear. I had to talk to him. Maybe if I just fucked him once, I could get it out of my system. I had to do some research first.